


I'd Rather Laugh With the Sinners Than Cry With the Saints

by jensenisafallenangel



Series: Only The Good Die Young [2]
Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Modern Setting, Bisexual Dean Winchester, Boys Kissing, Explicit Language, Explicit Sexual Content, First Dates, First Kiss, First Time, First Time Blow Jobs, John Winchester's A+ Parenting, M/M, Naomi Being a Dick, he redeems himself
Language: English
Status: Completed
Published: 2016-11-23
Updated: 2017-04-08
Packaged: 2018-09-01 16:14:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,491
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8630689
Author URL: https://archiveofourown.org/users/jensenisafallenangel/pseuds/jensenisafallenangel
Summary: With his talent show performance, Dean convinced Cas to go on a date with him and he really doesn't want to mess it up.





	1. Chapter 1

The night after the talent show, Dean drove to Castiel’s house to pick him up for their date. He had driven there countless times before but this was indescribably different.

Dean parked and thought to himself that he had felt more prepared to go up and sing in front of the entire school. This felt fragile and like much more was at stake. Embarrassing himself in front of the school would be preferable to screwing this up with Cas. 

At the front door, Dean rang the doorbell and only had one fleeting moment of panic before Cas opened the door quickly. He was wearing a sweater vest just like Dean had requested and he looked good.

“Eager are we?” Dean joked with a smirk.

Cas blushed and looked down. 

“I’m kidding,” Dean smiled, “I’m excited too. Let’s go.”

Cas visibly relaxed, his shoulders less tense and with a shy grin on his face.

The drive there was pleasantly quiet with just a little bit of small talk. Dean couldn’t help a tiny sigh of relief that it wasn’t awkward and Cas already seemed to be enjoying himself. 

The restaurant Dean chose was nice but affordable. If he had the money, there were many better places that he would have taken Cas to but this would have to do. 

“I’ve been here a few times,” Cas remarked as they sat down. “They have delicious burgers.”

Damn if Dean didn’t want to kiss him right there in front of the packed restaurant. 

The two got drinks and each ordered burgers.

“So, rumor around school is you have a large family,” Dean said, sipping his Coke as they waited for their food. 

“People talk about that?” Cas asked, eyebrows furrowed together.

“No,” Dean admitted. “But I might have asked around about you.”

There was no way Cas could have hid his blush from Dean if he tried. 

“Um,” Cas answered. “It is big, my family. I have five siblings and cousins that are around enough to be like siblings.”

“Wow,” Dean replied, eyes wide. “I just have Sam.”

The waitress dropped off their food and both said thank you without looking away from each other.

“You two are close?” Cas asked, digging in to his burger.

“Very,” Dean said, mouth full of burger.

Immediately, he regretted talking with his mouth full and being gross but Cas’s small smile made it seem like he didn’t mind.

They talked a little about school but Dean switched from that pretty quickly. He didn’t need Cas to know how dumb he was. He’d be lucky to graduate on time.

“Any movies out that look good?” Dean asked.

“I don’t usually go to the movies,” Cas replied with a shrug. “Why?”

“I was thinking of,” Dean started. “We could maybe, um…”

Cas was patient, letting Dean figure out how to ask.

“Maybe that could be our second date?” Dean asked, looking up on the last word.

“Sure,” Cas agreed.

“Really?”

“Only if you’re as good at second dates as you are at first ones,” Cas complimented.

Finally, Cas got to Dean to blush. 

Once the check came, Cas tried paying for his meal but Dean insisted on paying.

“You really don’t have to…”

“I did the asking, I’ll do the paying,” Dean reasoned.

“Fine,” Cas gave in. “Then I’m officially asking you to the movies on Tuesday night and I’ll pay.”

“Deal,” Dean smirked.

The bill was paid and the two left.

At Cas’s front door, Dean walked Cas up to it.

“You know I’m not a girl from the 1950’s, right?” Cas sighed.

“I’m being a gentleman, Cas,” Dean commented. “Even though you never thought I could be.”

“I never said that,” Cas tried.

“You definitely implied it then,” Dean pointed out.

“I had a nice time, okay?” Cas said, immediately placating Dean.

“I’m glad,” Dean grinned. “Me too.”

Dean knew Cas never had his first kiss and this felt like the moment but Dean doubted himself. He clenched and unclenched his fists inside the sleeves of his leather jacket. There was a pause before both started to lean in but at the last second, Dean simply placed a kiss on Cas’s cheek. 

“Good night, Cas,” Dean said quickly, afraid he did something wrong. 

He looked back only when he was in the driver’s seat ready to leave but saw Cas’s smile and blush and knew he didn’t mess it up.

 

At school on Monday and Tuesday, the two of them acted friendly as they always had. There were plenty of comments about the talent show where Dean sang Billy Joel to Cas but both played it off like it was nothing. Truth be told, neither liked the spotlight much. 

Tuesday night, Dean was parked in Cas’s driveway ready for the second date. Cas made sure Dean knew that he was taking him out this time and he would be paying but he just didn’t have a car.

There had been a pretty long conversation over texting throughout the weekend about which movie to go see. Their options were a romantic comedy or an action movie. Dean argued they weren’t girls so romance was silly but Cas reminded him it was a date so romance was perfect. Cas also pointed out that he did the asking so he had the ultimate say when Dean kept arguing. 

So Cas bought them tickets for a chick flick without even noticing the weird look from the person who sold them. Dean glared for both because he didn’t appreciate the judgmental crap. 

They both agreed popcorn was a must and then went to find seats.

The movie hadn’t been out long but it was a Tuesday night so it wasn’t too crowded. The boys had the entire row to themselves and they laughed at the previews for some upcoming movies that looked pretty bad.

“Maybe we can come see one of those and make fun of it,” Dean suggested.

“Sounds good to me,” Cas replied.

If Dean had been with anyone else, he wouldn’t have admitted that he kind of liked the movie but this was Cas. Halfway through, he leaned over to whisper that it had been a good choice.

“I’m glad you like it,” Cas grinned.

Dean put the empty popcorn tub on the ground and glanced at Cas’s hand on their shared armrest.  
Would holding it be too much? He really wanted to hold Cas’s hand but wasn’t sure what his response would be. 

Screw it, he thought.

With no attempt to be subtle, Dean put his hand lightly on top of Cas’s. Cas had space to flip his hand over and intertwine their fingers. Cas had a small smile that Dean almost couldn’t see in the dark theater. 

Internally, Dean was fist-pumping and hollering but externally he just let out the breath he had been holding.

They kept holding hands through the rest of the movie and on the walk to the car after it ended. 

“I really like spending time with you, Dean,” Cas said as they pulled into his driveway.

“Same here,” Dean said. “I mean, I like it too. Spending time together, I mean.”

He let out a laugh and got Cas to smile despite his awkward attempt at speaking words. 

“I like spending time with you and I’m pretty lucky you finally said yes to me,” Dean managed, not one to usually chat about his feelings.

“I’m lucky myself since you agreed to go another date with me,” Cas shrugged.

“Of course I did. Why wouldn’t I?” 

Cas just shrugged again.

“It’s late, why don’t I walk you up?”

Cas nodded and the two walked to the front door. Dean was determined not to be a chicken shit this time and finally give Cas his first kiss. He just wanted to make sure it was perfect. 

“You know you’re awesome, right?” Dean asked, a little worried about Cas and his apparent lack of knowledge of that fact. 

“I am?” Cas replied, eyebrows furrowed and head tilted to the side.

“Yes,” Dean answered with finality.

Cas looked grateful to hear that and was maybe going to say something but Dean leaned in and gently pressed their lips together. 

Dean didn’t let it last long since he didn’t want to overwhelm the guy. 

“Not bad for a first kiss,” Dean praised with a smirk. 

“Uh,” Cas answered without his usual wit. 

Dean let out a soft laugh, thrilled he could be the one to kiss Castiel Novak for his first time and leave him speechless.

“I’ll see you at school tomorrow, Cas,” Dean said.

“Okay,” Cas agreed. “Thank you.”

“For what?” Dean asked.

“Everything.”

Dean smiled.

“My pleasure.”

 

A week after their first dinner date, Dean was taking Cas out to dinner again. He worked doing some odd jobs around his neighborhood and so he could take Cas to a nicer place than the time before.

“You know I’m fine just spending time with you, it doesn’t have to be fancy,” Cas pointed out when they sat down.

“I know. I agree with you,” Dean said. “but I like being able to take you somewhere fancy. I want to treat you right, make you feel special.”

Cas only smiled and blushed. 

They kept talking and getting to know each other. Cas really liked art and wanted to go to college. Dean shared about how much he worked on his car to keep her in such good condition.

After they ate, Dean suggested they walk around. After bumping their hands together a few times as they headed towards an ice cream place, Cas got the hint and laced their fingers together. 

They ordered their ice cream, chocolate for Dean and vanilla for Cas. Dean somehow managed to keep his jokes to himself about Cas’s choice as they sat down. 

“You got some on your face,” Cas said, gesturing towards Dean’s chin. 

Dean used a napkin and tried to get it.

“Good?” Dean asked.

He somehow managed to miss it entirely which greatly amused Cas.

“Nope,” Cas laughed. “Let me.”

Cas reached across the table to clean the ice cream from Dean’s face.

“Thanks,” Dean said, feeling his cheeks get warm.

“Of course,” Cas replied. 

Once the date was over, the two again were on Cas’s porch. 

“So, three dates,” Cas reminded Dean. 

“Yeah,” Dean smirked. “They’ve been great.”

“They have,” Cas agreed.

He paused, seeming unsure of what he wanted to say next.

“What is it?” Dean questioned. 

“Can I ask you something?” Cas asked.

“You just did,” Dean teased.

“Cute,” Cas said, rolling his eyes but smiling.

“For real, though, you can ask me anything,” Dean noted.

“Are we dating, like boyfriends? Is that what we are now? I was wondering and it’s fine if you don’t want…” Cas rambled.

Dean stopped him by kissing him. It was longer and better than their first kiss because Dean wasn’t holding back as much. He pulled Cas in by his waist and deepened the kiss. Cas ran a hand through his hair and relaxed into Dean, seeming comfortable like they had been doing this forever.

“Wow,” Cas said softly when they finally paused for air. 

“Now you get the good stuff because you’re my boyfriend,” Dean grinned.

“Really? You’re sure you want that?” Cas asked, still doubting how awesome he was.

“I was the one who kept asking you out, aren’t I?” Dean recalled. 

“Yeah,” Cas sighed. “You are. And I’m glad you did.”

Dean gave him another kiss and then said good-bye. 

 

Two days after their second dinner date, Dean picked Cas up from church after an urgent text to save him.

“Thank you for rescuing me,” Cas said as he got into the Impala. “I don’t think I could have made it through another luncheon with everyone’s holier-than-thou attitudes.” 

“That’s what I’m here for,” Dean joked. “Rescuing you only to lead you down a dark path of temptation and sinning.”

Cas’s jaw dropped a little at the suggestiveness but Dean simply winked and they drove off to the Novak house. 

“So, no one is going to be home for a while?” Dean asked as they walked into Cas’s kitchen.

“Right,” Cas said, nudging Dean with his shoulder. “But get your mind out of the gutter. I need to eat lunch.”

“Okay, okay!” Dean laughed. “I could eat.”

The two of them made sandwiches, grabbed chips and Cokes and went to the living room to put on a movie. 

It could have been a comedy or a horror movie, Dean had no idea. He was so distracted by Cas sitting so close to him. Impossibly close and Dean had to keep his mind away from dirty thoughts but it was not working.

When they finished eating, Cas cleaned the plates and cups away. He came back and sat even closer to Dean.

“Are you okay?” Cas asked, eyebrows furrowed.

“Yeah, fine,” Dean said, not looking at him.

“You seem tense,” Cas observed. “How come?”

“You.”

“Me?” 

“You’re really close and hot and I want to kiss you,” Dean said in one breath.

He looked over at Cas who was staring at his lips.

“Go ahead then,” Cas said.

“You sure?”

“I mean, if you don’t want to,” Cas teased.

Dean leaned in and kissed Cas, their first not standing out on the porch. He reached a hand up to brush Cas’s cheek and then ran it through his dark hair.

Cas leaned back and Dean followed, continuing to explore his boyfriend’s mouth with his own until Cas was on his back.

“You’re okay?” Dean asked, tentative to not push Cas too fast.

“Yes,” Cas assured him.

They kept making out until Dean knew he couldn’t pretend he wasn’t hard anymore. To be fair, Cas felt pretty turned on too but Dean jumped back.

It was silent for a beat as they sat side by side.

“What’s wrong?” Cas wanted to know.

“Absolutely nothing,” Dean said truthfully. Making out with Cas was great.

“Then what? I know you’ve been holding back, Dean,” Cas accused. 

“I don’t want to push you or go too fast,” Dean admitted.

“That never stopped you with anyone else,” Cas said, crossing his arms over his chest.

“Well, no. But you’re not like anyone else, Cas,” Dean reminded him. 

Cas placed a gentle hand on Dean’s cheek to turn him to look at him.

“I promise I’ll let you know if it’s too fast, okay?” Cas said softly. “I trust you.”

“Okay.”

“Can we keep making out then?” Cas asked.

Dean laughed.

“Hell yes.”

So, that’s what they did until Cas’s mother came home from her church luncheon.

Both scrambled to put the shirts they had taken off back on as the key in the lock turned.

They sat in tense silence, far away from each other on the couch, as Cas’s mom walked in. She looked as uptight as she was, a high bun of brown hair and stern eyes. 

“Mom, you remember Dean?” Cas asked tentatively. 

“Oh yes,” she said icily. “The songbird from the talent show who wants to sleep with my son.”

 

TO BE CONTINUED


	2. Chapter 2

“So,” Dean greeted Cas’s mom uncomfortably. “nice to see you again, Mrs. Novak.”

Instead of answering, she looked Dean up and down in a rather cold and calculated manner that made him squirm.

“What were you boys doing?” she asked.

“Studying,” Cas lied.

“What subject?”

Cas said history at the same time Dean said physics. Those were the only two classes they had together and it was an unlucky break to pick opposite of each other.

“As if there are even books on the table in front of you. Good try, though,” Mrs. Novak stated simply. “I’m going to start dinner. I trust your friend has to be going home to his family.”

Dean hated the way she said family, like his was so filthy, but she walked away and Cas put a hand on his arm to calm him. 

“Maybe…”

“Don’t worry, I’m gone,” Dean agreed. “Text me in a bit, okay?”

“Sure,” Cas agreed. 

Dean gave Cas a quick kiss before he slipped out the front door.

He drove home and quietly walked past his father who was passed out on the couch to the room he shared with Sam. 

“What’s up?” Sam asked as Dean flopped on his bed.

“Was with Cas,” Dean replied. “Dad move at all?”

“Nope.”

Their father had been there since coming home last night and apparently hadn’t woken up yet.

“Oh well,” Dean shrugged. 

His phone buzzed and he looked to see a text from Cas.

**Cas: She didn’t kill me**

Dean let out a small laugh.

**Dean: Thank goodness. I still have more dates to take you on**

**Cas: What did you have in mind?**

**Dean: End of the year carnival**

**Cas: Sure, if my mom ever lets me out of the house again. Her exact words were that she still disapproves of that Winchester boy.**

**Dean: She thinks I’m a bad influence? ;)**

**Cas: Yes**

**Dean: I’m guessing you didn’t tell her we kissed**

**Cas: And I know you didn’t tell your dad**

**Dean: Fair point**

**Cas: See you at school tomorrow?**

**Dean: Yeah I can’t miss any more days**

**Cas: That’s why my mom thinks you’re a bad influence**

**Dean: Haha. See ya Cas**

**Cas: Bye Dean.**

The two of them cooled off on their dates for a while to avoid crap from their parents. While Naomi Novak was a much more involved parent than John Winchester, the boys knew neither would be happy with them dating.

Luckily, they could see each other all the time at school where their parents could remain ignorant of their involvement. The change in how Dean and Cas acted was subtle but their closest friends like Charlie and Kevin, noticed.

“You two are so sappy,” Charlie pointed out at lunch.

“How?” Dean asked. “We’re just eating.”

“It’s the subtle looks,” Kevin said through a mouthful of food, “when you think the other isn’t looking.”

At that, the two did look at each other before smiling and looking away.

“Shut up,” Dean grumbled.

“Don’t get grumpy because we’re right,” Charlie laughed.

Dean just rolled his eyes and if he wasn’t such a coward, he would have tried to hold Cas’s hand under the table but Dean knew Cas still cared what the school thought even if he didn’t want to. 

 

It was the end of the school year and the annual carnival fundraiser was set up. Dean had texted Cas a time to pick him up on a warm Friday night in May and they were set for another date.

Dean felt them getting more comfortable with each other every time they hung out. They could just talk and be themselves which Dean wasn’t used to. Anything previous had just been meaningless hook-ups. This was new territory for them both.

“All right,” Dean said as they walked into the carnival. “What should we do first?”

“We could play a game?” Cas suggested.

“Sure,” Dean agreed.

The boys tried to ignore the stares and confused looks as they walked through the carnival. At school was one thing but parents were here and they all knew John and Naomi. Dean started to worry about Cas’s reaction but when he glanced at him, he seemed relaxed.

“You okay?” Dean asked.

“Yes,” Cas said with confidence. “If the one thing I learn from you is to ignore what people think, I’ll be lucky.”

Dean didn’t know what to say so he just pointed out a game that involved shooting a fake rifle at a target. There was a big stuffed bear he wanted to win for Cas.

Cas tried not to laugh as Dean kept getting more frustrated trying to win the damn game. Many dollars later, Dean finally won and did a dorky happy dance.

“Thank you, Dean,” Cas smiled. “I love it.”

The two of them went on a few of the rides like the Tilt-A-Whirl, made out on the Ferris Wheel and grabbed some hot dogs and funnel cakes before calling it a night. As they walked out to the parking lot, three of the worst people either of them knew were walking towards them.

Dean and Cas were all set to ignore Crowley and his douchebag friends, but they didn’t get off that easily. 

“Hello, boys,” Crowley said. “Out on a date, are we?”

“None of your fucking business,” Dean snarled.

The two of them regularly fought, something about sleeping with someone’s girlfriend, neither could really remember the cause of the resentment now. It was just understood that fists would start flying if they stayed.

“Aw, he won his little boyfriend a teddy bear,” Alastair jeered.

“Listen, you piece of shit…” Dean started.

“It’s not worth it,” Cas interrupted. “Let’s just go.”

“Yeah, better go before we kick your ass,” Crowley agreed.

As much as Dean wanted to take all three of them on, the look on Cas’s face was pleading for him to drop it.

Without another word, Dean and Cas walked away. Their taunts and comments called after them almost caused to Dean to run back but Cas insisted they leave.

In the Impala, Dean started it and had a death grip on the steering wheel but didn’t start driving.

“You okay?” Cas asked.

“Fine,” Dean lied. “I’m fine.”

He was glaring out the window at nothing and still gripping the wheel tightly. 

“You don’t seem fine,” Cas called him out. 

“I… just really hate those guys. Reminds me how my dad is, just not being okay with who I am,” Dean admitted.

Cas just nodded. He took Dean’s hand and gave it a squeeze. 

“You know those idiots don’t matter, right? And your dad could change his mind. Someday. Crazier things have happened,” Cas tried, attempting to provide some comfort. 

Dean let out a deep breath.

“Can we go somewhere else?” he asked.

“Sure,” Cas said. “My mom is at a church thing, like always. I lied to get out of it. We can go to my house.”

Dean started to drive, staying quiet.

Inside Cas’s house, Dean was led upstairs by his boyfriend to his room. Looking around, it felt plain.

“Not much of a decorator?” Dean joked.

“My mom pretty much only let me put up the cross above the door,” Cas shrugged.

Dean glanced at it and was distracted enough for Cas to surprise him with a kiss. 

“What was that for?” Dean grinned when they broke for air.

“Thanking you. For our date tonight,” Cas said.

“I’m sorry I almost got into a fight,” Dean said, eyes downcast. “They could have hurt you…”

“It’s okay,” Cas said, stroking Dean’s cheek with his thumb. “We’re okay.”

Dean rested their foreheads together and pulled Cas closer.

“We’re okay,” he repeated.

Cas kissed him again, long and thorough. It was full of so much tenderness that Dean’s knees were weak and he felt tears prickling in the corner of his eyes. 

Cas led him back to the bed. He guided Dean over him as he laid on his back and pulled Dean’s mouth back to his own.

Dean ground his hips down without thinking and felt Cas getting hard under him. He kissed down Cas’s neck gently before leaving a hickey under the collar of his shirt. 

“Dean,” Cas groaned. 

Dean went back to kissing Cas’s delicious lips and moving his hips. He wasn’t sure how far Cas wanted to go, but he knew he would stop him if he wasn’t ready.

“Dean, I want to touch you,” Cas said, barely above a whisper, “Please.”

Cas, at Dean’s nod, flipped them over. He moved his lips like Dean had done and seemed pleased with the moan he got in return. His hands went to the fly of Dean’s jeans and slowly undid the button and zipper. Dean lifted his hips enough to let Cas work his cock free.

“Beautiful,” Cas said, looking at all of Dean, eyes moving every inch.

“Yeah, yeah,” Dean rolled his eyes. “You jerking me off or what?”

Cas glared.

“I think you are beautiful. Inside and out.”

“You’re not too bad yourself, Cas,” Dean joked.

Cas draped himself over Dean, teasing barely enough friction on Dean’s cock, before fiercely kissing him.

“Do you agree you’re beautiful?” Cas whispered in Dean’s ear before taking his earlobe between his teeth.

“If I say yes, will you touch me?” Dean asked.

“Only if you mean it,” Cas replied, looking into his eyes.

“Fine. I am one fine piece of ass. Now, please…”

Cas carefully wrapped a hand around Dean and moved it up and down.

“Oh, shit,” Dean said, dropping his head back.

Cas took his hand off only long enough to lick it to get some lubrication. 

“Damn, sweetheart, where did you learn that?” Dean asked. 

“Internet.”

“Porn?”

“Quiet and let me finish,” Cas snapped.

Dean’s laugh died as Cas used his other hand to massage his balls.

“Fuck,” Dean let out. “Fuck, Cas. Faster.”

Cas didn’t have to work much harder before Dean was spilling over Cas’s hand. Cas grabbed a tissue from the bedside table and cleaned his hand off and the little bit that got on Dean’s shirt. 

“Cas, that was…wow.”

Cas smirked.

“Your turn,” Dean smirked in return, flipping Cas on his back.

He worked Cas’s pants down before looking up.

“You’re okay?” Dean asked.

“Yes,” Cas answered.

Dean took Cas in his hand and did the same trick with the spit-slick hand and didn’t ignore the balls. It didn’t long for Cas to come, shouting Dean’s name.

“Wow is right,” he grinned, still catching his breath. 

Dean wanted more than anything to fall asleep with Cas next to him, hearing him breathe and knowing he was safe, but Naomi was going to be home soon. 

“I hate to go but…” he started.

“I’ll see you at school Monday?” Cas asked.

“Yeah,” Dean said with a final kiss. “I’ll text when I’m home.”

“Bye Dean.”

“Bye Cas.”

Dean drove home with a silly grin on his face that died when he walked through the front door of his house. His father was standing there, arms crossed and looking pissed. The man seemed mostly sober, a shock, and Dean didn’t like where this could be headed.

“Dad? What’s up?” 

“Why am I hearing you took my car to take a boy on a date?” John snapped.

“I didn’t take anyone on a date,” Dean lied. “He’s a friend, we were bored and the carnival was at school. We went looking for girls to hook up with.”

John weighed the validity of that excuse and must have bought it. He dropped his arms and Dean tried to not look too relieved.

“Good,” he nodded once. “You worry me, son. I can’t have someone like that in my house.”

Dean didn’t say anything, just let his dad walk out the door to go drink.

He went to sleep without texting Cas.


End file.
